Living His Fantasy

Lane took a deep breath, his palms sweating. Every Saturday night now, for the past 7 weeks, he's been renting a hotel room. He paid for them in advance, and always got the same one; at the end of the hall, on the corner of the building so that he shared less walls with the neighbors. Room 3002. It had a view, oh, a spectacular view at night. He was afraid of heights, but that's what made his self-bondage so exhilarating.

During the day, he was the CEO of a medium sized company. They employed about 700 people total. But when he got home, to an empty house, he fantasized about being humiliated. He harbored so much control over the company and peoples lives at his 9-5 but ached for control to be taken.

He dropped his overnight bag on the table and pulled his tie loose. He undressed, leaving on his black work socks, and pulled a short expandable bar and a chain from his bag. Each had a leather cuff on each end. Moving to the DVD player, he slid in a DVD of a compilation of various audio of women spanking their submissive men; the first on the DVD started with a hard crack, and a deep, guttural cry of discomfort. Within five minutes, he knew, he would begin begging. Sometimes the women would show mercy, others would increase the spanking. He knew the difference between the sound of a paddle and the sound of the smaller wooden spoon or brush, and the sound of a cane, and the sound of a flogger and the sound of a whip. He liked the wooden spoon or brush best. The crack was sharper, and it often made them hiss.

He'd never felt one, though. He grew up with the privilege of a nanny who cared for him and she would spank his rear with her hand at most 3 times. He realized he liked it when she did it when he was 14. But she would never give him more than 3 swift swats.

Approaching the windowsill, he knelt up on it, feeling lightheaded as he felt as if he was going to tip out the window. He hung the chain over the curtain rod and reached down to place the first cuffs of the spreader around his lower thighs. He clicked them apart until his knees were spread 2 feet apart. He pulled 2 items out of his pocket; a timed padlock and a bullet vibrator with a band to hold it on his dick. He set it to medium, with pulses, and slid it onto his hardening cock. The first long buzz coincided with a crack on the DVD audio, and he moaned as the man from the speakers whimpered. His cock jumped, and he felt a shiver run up his spine. Quickly, he cuffed his hands and locked them together, setting the timer for 1 hour. He used a hair clip to hang the keys from the curtain beside him, just in case.

Today had been particularly frustrating. His secretary had decided to take her lunch standing beside her desk, coffee in hand, resting her bum on the edge of the stained wood. She leaned on her hand, her long fingers wrapped around the lip of the desk, long red nails grazing the wood. He's always liked his secretary. He didn't hire her, so he didn't feel guilty about her getting her job because his dick got hard thinking about her long fingers wrapped around the carved handle of a wooden brush.

He relaxed, imagining that someone... maybe even someone he knew, had happened to scan the windows of the hotel with binoculars and was watching him bound, gyrating at the stimulation, moaning in time with the audio and imagining it was his ass being turned red from the punishment these dominant women dished out.

Nearly 20 minutes later, he came, semen jetting from his cock onto the window. But he would remain locked for no less than 40 more minutes, and the vibrator still worked the head of his cock. It almost went limp for a second but picked back up quickly when it realized there was still more to do. Plus, the sight of his semen running down the glass and pooling on the window sill made him pant and groan in anticipation.

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The lock clicked open and he slowly unraveled himself from his self-bondage. He winced as he brushed against his now overly sensitive cock. With no interest in spanking himself, this was his next best punishment. For the past 7 weeks, he's been refraining from self-pleasure and only ejaculating in this room. He felt as he didn't have permission to come like he wanted, he'd torment himself afterwards and force more orgasms on himself without waiting. It was a painful process, but one he was addicted to.

But oh, what he wouldn't give to have a woman spank him! He wanted to feel the heat of a cherry red ass. Getting down from the windowsill, he picked him his phone and scrolled the web, posting on a forum to ask where the best place to get quick local sex through an app was. He quickly downloaded a few and came to the quick conclusion that he didn't want to use the fetish sites. His groin stirred, though his tired cock remained flaccid, at the idea that a woman expecting free vanilla sex come in and be confronted with his desires. He signed up and was immediately allowed to apply to the classifieds.

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He was laying in bed, and it wasn't until 4 hours later he received a ping. The girl was pretty, and it looked like an average photo, not one of a women trying too hard or using a fake photo. But hey, you never know. He decided to risk it.

He was in a private message with the woman for about 20 minutes before she offered to meet up. He said, "sure" not wanting to sound too eager. He told her he had a hotel room for a business trip, and he would love to meet her. He would slide a keycard in an envelope under the door so that it poked out just enough for her to grab. "Just in case I'm in the shower and can't get the door." He justifies. While he was messaging her, 3 more women tried to speak with him, but he put them on hold.

He was taking a huge risk here. Several things could happen. First, housekeeping could walk by, see the envelope, take it and try to enter the room to return it. That would be bad. Second, another resident could do the same. Third, she would come in, see him in the position he would choose, and leave because he was a freak. Somehow the idea excited him.

Lane shut the TV off and shoved the DVD in a drawer. Next, he raided the kitchenette and found a wooden spoon; one of the reasons he loved these hotels, and placed it at the foot of the bed, scribbling a shaky hand-written note "Spank me, Please". He took the note and the spoon and grabbed a chair, bringing it into the foyer out of view of the bed, and placed the spoon and the note in plain view. He put his extra keycard in an envelope and slid it under the door until the corner peeped out, then he propped himself up on the pillows, ass in the air, cock and balls tucked down and in plain view. He installed the spreader bar, but left his hands free, simply stretching them out in front of him.

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Lane waited, and in a half an hour, he heard the envelope slip out from under the door. His heart was pounding. This was it. His half-baked foolish plan was coming to fruition and there was no backing out of it now.

He heard heels in the foyer, and a pause, and a shuffle of paper. His cock twitched, imagining his written words on the confused lip of the pretty face he saw on his phone. He heard a soft, unfamiliar voice, "The fuck..." she whispered, and her heel clicks became muffled on the carpet.

"Oh my god..." she said, and his face, shoulders, and ears turned red. He felt beyond humiliated, but his cock remained hard as a rock, restricted by the pillows under him, pointing straight down. A wet spot formed right below. He clenched his teeth and said nothing. "You seemed so fuckin normal. Of course, my luck! A bondage freak." She threw the spoon down on the bed, and he imagined her propping her hand up on her hip, shoulder length mousy brown hair framing her face. She stood there, waiting.

He took a deep breath, and with a shaky voice, he spoke, "I'm sorry to have mislead you, Ma'am. I-I could pay you, just please, c-can you s-spank me?" He felt humiliated, not having meant to offer compensation, but it just slipped out. He was desperate. His voice was muffled against the comforter.

She tapped her fingers against her thigh, biting her inner lip. Paid to spank a freak? She turned to leave, but then paused. What harm would it do? She was out of town, he hasn't looked at her face... She pursed her lips. "Do you like to be blindfolded?" she asked him, and he told her he didn't mind, and it it made her comfortable she could use his work tie. She found one on the back of a dining chair and approached him. "Don't look." He clenched his eyes shut obediently, and she wrapped the tie over his eyes. He shivered at the feel of her nails against his face. She tugged the makeshift blindfold down against his cheeks. "So, how often do you do this?" she asked him, inspecting the wooden spoon.

He bit his lip, unable to believe he'd found a willing, albeit reluctant, participant in his fantasy. "N-never... No, I swear!" he said when he heard her scoff. "I-I've been coming here for awhile and tying m-myself up but... I've never been spanked before. I don't have a girlfriend, I've never spanked myself." He trailed off and shifted on his knees.

She bit her cheek, and tilted her head, looking at his propped-up ass, the musculature of his back, and the tone of his legs. He wasn't a bad looking guy, and going by the tie, and his clothes hanging over that chair, he wasn't bad off either. But a submissive kind, well, that might keep him from keeping a girl. Or getting one, she thought.

She approached him. "I'm going to do three for now." He groaned inwardly, three is what his nanny always did. His cock twitched. He nodded. "I want you to count." She was nervous, but she figured maybe he should try and participate here. She raised the spoon, and cracked it across his ass, right in the center. His butt clenched, and he let out a tortured moan. Behind the blindfold, his eyes rolled, and he felt his thighs shaking. "O-one..." he panted. Oh, it was just as wonderful as he imagined. She cracked the spoon on him again. "Two!" he cried. The third came again, in the same spot as the first two. He was glad he used the spreader bar, because his thighs tensed, and he tried to roll to the side.

"Three!" he said breathlessly.

She furrowed her brow. "Wow, you really like that?" she asked him, putting the spoon down. He gripped the sheets in front of him as her weight indented the end of the bed, and he moaned loudly as she laid her nails on the slightly flushed skin. She jerked away from him when he did. "What, did that hurt?" she asked him, and he panted, shaking his head. "N-no... its good."

She reached out again, this time sliding her nails across his cheeks. He moaned again. "So, why do you use the spoon? Why not something bigger, like a belt?"

"D-do you want to try a belt?" he said, twisting his head towards her voice, his own raising an octave, a bit hopeful. His heart was pounding in his chest and his cock twitched. It had been his first ever spanking, and he needed more. Punishing himself, even with post orgasm stimulation just wasn't going to satisfy him anymore, he knew it. Her feelings towards him, the way she saw him as a strange freak, an oddity served only to turn him on.

She chuckled nervously. "I don't know about all that." She said, moving away from the bed. "I should probably go..." she stood slowly, but her eyes lingered on the belt still wound in the loops of his slacks.

"P-please! Please use the belt I-I'll be ok with that! I-I'll give you more money!" he said, his toes curling, forehead pressing into the bed, voice muffled a bit. Then he sagged, clenching his fist, his nails digging into his palm. "Just... just one go! I need more."

He was making an absolute fool of himself. All to be demeaned and humiliated by this strange woman. He was a CEO for Christ's sake! This was disgraceful! He fisted the sheets under his hands.

Then, he heard the rattle of a belt buckle. "Same as before?" she asked, feeling the leather in her palm.

He nodded, "H-harder... please..." he whispered. "A-And more... 10?" he offered, hoping beyond hope he wouldn't make her run.

She stood behind him, shocked at herself. Here she was, on a blind fuck date with a stranger and he was laid up on a bed, ass in the air, begging her to spank him. A grown man! She slid the leather loop through her fingers, only about 2 inches wide, looking at the pink fading on his ass cheeks. Something about this, however, was daring, exciting. She licked her lip and rubbed her knees together. God... was she turned on from this?

"No..." she said, watching him deflate. "20 will do."

If this man could have creamed himself then, he would have. His butt clenched, his hips ground into the pillows under him and he let out a loud moan. "Yes please..."

"Why?" she asked him.

"W-why?"

"Why am I spanking you? What have you done?"

He couldn't help but smile. She was playing along, getting into it. He bit his lip, not one for roleplay. He wanted her to beat him for things he'd actually done. "I... I book this room every weekend to tie myself up and tease myself, fantasizing of..." he hesitated, "Fantasizing about you."

She smiled slightly. If he wished to be punished because of his perverted tendencies, she would oblige. She pulled her arm back and cracked the belt hard across his ass. He yelped, jumped, and his hips thrust against the pillows. "Of me?"

"YES!" he said loudly, mouth open against the bed, panting. "Someone like you... W-who would punish me." She cracked the belt, making an X of red marks. "Wh-who would punish me for giving a strange woman my hotel key, for leaving it for anyone to find!" Another 3 cracks. His ass cheeks wobbled as he tensed, gyrating his hips from the pain. He had lifted his torso, his knees taking his weight. His feet jittered, trying to take the pain. 3 more strikes. This time, well aimed at the tops of his thighs, straight across. He felt the last one lick his balls, and he shot upright, his back concave as he covered his ass with his hands. But she was already mid swing and left a welt across the backs of his strong hands. He jumped, wringing his hands, a hiss escaping. But touching his ass again, he moaned softly, cradling his striped welted behind, softly sobbing into his blindfold.

"Would you like me to stop?" she asked softly.

"I c-can't... th-the punishment isn't finished." He whispered. "Th-that was 8..." He didn't count the one that landed on his hands. What a glutton for punishment.

"We can't have your hands getting in the way..."

"I-I have c-cuffs... a-and a chain..."

She turned around to pull them from where they lay on his overnight bag. She cuffed him and wound the chain around the spreader bar. Now, he would sit entirely upright, but he couldn't reach his behind. He laid back down on the pillows, adjusting. His cock pressed between the pillows and his abdomen now, and he felt how slick it was. He slowly ground into it, welcoming the friction.

"Why am I spanking you?" she asked again. She felt her clit throb. She didn't want to admit how wet this was making her. When she rubbed her thighs together, they were slick.

"I-I interrupted the punishment, Ma'am..." he whispered, bracing for the next impact, it crossed his upper thigh, and he jumped, yanking on the chain, but it snagged on the bar and his hands went no further than his navel. His torso shuddered, and he moaned at the restriction. He felt as if semen rose in his shaft for a moment.

This... this was everything he fantasized about. She landed two more strikes as he disappeared into his mind, feeling like he was floating on clouds. This woman, though he had not seen her face, was the most beautiful thing in his suddenly small and meaningless world now. He wasn't sure if her panting was from arousal or exhaustion, but he imagined her relishing in this. He wanted to do anything for her. He hoped she wanted compensation other than a bit of cash, because oh god, he was happy to give it to her. He moaned aloud, tears soaking his tie as his body trembled from the pain in his ass, radiating down his thighs. And yet his arousal raged. The next strike landed, and clipped his balls again. He yelped, bolting almost upright precum flinging in a string across the pillows in front of him. Lane yanked so hard at the chain that the cuffs dug into his thighs.

"You made me wait." She said, delivering # 13.

"Yes Ma'am, I'm sorry!" He sobbed. He sounded genuinely sorry, as if this was a true crime that he was being punished for. "I'll be good, I'm so sorry!"

She didn't speak again. Instead, she imagined his head between her legs as she laid 7more in quick succession on his ass, sending him into a frenzy, thrashing side to side to alleviate the pain. She paused, panting, her arm a bit sore. She felt she went overboard; his ass was not even red anymore, there were raised welts from the edge of the belt and some were pale, and others were starting to turn color. She dropped the belt on the bed and took a deep breath. She retreated to the sink, each step causing moisture to slick down her thighs. Her panties were soaked.

He heard the tap, and heard a glass fill with water, pretty lips taking a sip, sighing. She looked over at him as he is shifting on the bed, whimpering. Maybe she had gone too far, she thought. But no... he was smiling. IT wasn't a big 'ole grin, it was just a slight upturn of his lip on the side she could see. He swallowed heavily, and opened his mouth against the comforter, a sudden twitch going through his body as the pain radiated again. He bit the cover.

She sat on the bed against the headboard and guided him to sit more upright. He winced, his ass on fire, and she uncuffed his wrists and removed the spreader bar. She hiked her dress up and spread her legs. "For whatever fucking reason..." she whispered, grabbing a fistful of his hair and dragging him up the bed. He willingly obliged, scrambling on all fours. "This whole thing has me so fucking turned on. You're a sad, sick fuck." She snarled, and he turned red. The demeaning language she used made him shake. His cock stood jutting straight at her. "I'm sorry, Ma'am." He said, clenching his fists at his sides. He did everything in his willpower to avoid touching his rear. But oh, he wanted to. He imagined how cool her fingers would feel.

The woman paused, shifting and pulling her panties down, leaving them hooked around one ankle. She pulled him towards her cunt, but she had no need to tell him what to do. HE could smell the musk, the sweet nectar that oozed from her pussy and he groaned, practically diving between her legs. He slurped up along her labia, before he found her clit, lapping at it like a thirsty street mutt. He fell flat on the bed as he wrapped his arms around her thighs, holding her soft thighs against his body, he ferociously ground his cock into the bed below, hearing her moans. Her legs wrapped over his shoulders and she settled back, gripping his hair and the headboard. She wasn't sure if it was because she was just plain horny or if he was just that good, but he was good! She ground against his face, hitting her first orgasm within minutes, and her second just a few seconds afterwards. His own orgasm followed, and he ground heavily into the comforter his red bruised ass cheeks clenching and shuddering from the resulting pain which only served to fuel his intense orgasm. He was groaning right along with her. Her thrashing and his orgasm didn't stop him, and he shifted his position slightly to fuck her pussy with his tongue, his nose rubbing her clit into bliss.

After a few minutes of absolute and total release, she shoved him away, and he almost rolled onto his back beside her, but was reminded very sharply of his punishment. He hissed and tried propping himself up on his elbow and knees. Still blindfolded, he stayed that way, his head bowed, panting. He looked ridiculous with female fluids smeared all over his nose and face, making him look shiny, with a puddle of semen on the bed, and some of it smeared on his stomach. She chuckled, and went to the bathroom, taking a quick piss and drying herself off before plucking a pair of washcloths off the rack and wetting them, and grabbing a dry one for good measure. On her way out, she saw a sample of lotion on the sink, which she brought out as well.